US6613140B2 - Azo orange pigment composition - Google Patents

Azo orange pigment composition Download PDF

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Publication number
US6613140B2
US6613140B2 US09/954,237 US95423701A US6613140B2 US 6613140 B2 US6613140 B2 US 6613140B2 US 95423701 A US95423701 A US 95423701A US 6613140 B2 US6613140 B2 US 6613140B2
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Prior art keywords
rosin
weight
hydrogen
azo pigment
amounts
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US20020096086A1 (en
Inventor
Greig Chisholm
Sharon Kathleen Wilson
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BASF Corp
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Ciba Specialty Chemicals Corp
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Assigned to CIBA SPECIALTY CHEMICALS CORP. reassignment CIBA SPECIALTY CHEMICALS CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: WILSON, SHARON KATHLEEN, CHISHOLM, GREIG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B63/00—Lakes
    • C09B63/005—Metal lakes of dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/122—Developers with toner particles in liquid developer mixtures characterised by the colouring agents

Definitions

  • the present invention relates to a composition
  • a composition comprising
  • M is Mg, Ca, Sr, Ba, or Mn or a mixture thereof
  • R 1 , R 2 and R 3 independently from each other stand for hydrogen, C 1 -C 20 -alkyl, C 5 -C 20 -alkoxy, C 2 -C 20 -alkenyl, C 1 -C 20 -alkylthiol, C 1 -C 20 -alkoxycarbonyl, hydroxy-C 1 -C 4 -alkoxy, phenyl, benzyl, phenylthio, halogen, such as fluoro, chloro, bromo, iodo, cyano, nitro, —CF 3 , —COR 4 , —COOR 5 , —CONR 4 R 5 , —SO 2 R 4 , —SO 2 NR 4 R 5 , —NR 4 R 5 or —OR 4 , with the proviso, that—in formula III—when R 2 stands for hydrogen and R 3 is CF 3 , then R 1 is not —SO 3 ,
  • R 4 and R 5 independently from each other stand for hydrogen, C 1 -C 4 -alkyl or phenyl, with the proviso, that at least one of the groups R 1 , R 2 or R 3 is not hydrogen, preferably wherein R 1 is —COOH or —SO 3 H,
  • a resin selected from the group consisting of tall oil resin, gum rosin, wood rosin, hydrogenated rosin, rosin ester, disproportionated rosin, dimerised rosin, polymerised rosin, phenolic rosin and carboxyl containing maleic and fumaric resin.
  • Liquid inks are used mainly in the packaging industry where they are applied to a wide variety of substrates including paper, board, foil and polyethylene. Furthermore, such inks are also widely used in the printing of stationary materials, tickets, and comic books as well as other media.
  • EP-A 767 219 describes plastic compositions comprising a high molecular weight material and an azo pigment of formula V
  • M is Mg, Ca, Sr, Ba or Mn or a mixture of two or more thereof
  • R a and R b are chlorine or methyl
  • x is zero or 1
  • y is zero or 1
  • the sum of x and y is 1 with the proviso that when the high molecular weight material is polyvinyl chloride y is zero.
  • no pointer is given of how the compounds of formula V or mixtures thereof can be used in liquid ink applications.
  • no hint is given of how to increase gloss of an ink film and fluidity of an ink.
  • the object of this invention was to provide a novel composition, its use in liquid inks, especially for use in the packaging industry, a process for its preparation and liquid inks.
  • the liquid inks should have a superior fluidity, and should exhibit an improved gloss.
  • the pigment compositions preferably should be chlorine-free.
  • compositions were found.
  • a process for their preparation, their use and liquid inks, especially for their use in the packaging industry, have been found, too.
  • C 1 -C 20 -alkyl stands for methyl, ethyl, n-, i-propyl, n-, i-, sec.-, tert.-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, preferably C 1 -C 4 alkyl such as methyl, ethyl, n-, i-propyl, n-, i-, sec.-, tert.
  • C 5 -C 20 alkoxy stands for n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, n-dodecoxy, n-tridecoxy, n-tetradecoxy, n-pentadecoxy, n-hexadecoxy, n-heptadecoxy, n-octadecoxy, n-nonadecoxy, n-eicosoxy;
  • C 2 -C 20 alkenyl stands for ethenyl, n-, i-propenyl, n-, i-, sec.-, tert.-butenyl, n-pentenyl, n-hexenyl, n-heptenyl, n-octenyl, n-nonenyl, n-decenyl, n-undecenyl, n-dodecenyl, n-tridecenyl, n-tetradecenyl, n-pentadecenyl, n-hexadecenyl, n-heptadecenyl, n-octadecenyl, n-nonadecenyl, n-eicosenyl
  • C 1 -C 20 alkylthiol stands for methylthio, ethylthio, n-, i-propylthio, n-, i-, sec.-, tert.-butylthio, n-pentylthio, n-hexylthio, n-heptylthio, n-octylthio, n-nonylthio, n-decylthio, n-undecylthio, n-dodecylthio, n-tridecylthio, n-tetradecylthio, n-pentadecylthio, n-hexadecylthio, n-heptadecylthio, n-octadecylthio, n-nonadecylthio, n-eicosylthio;
  • C 1 -C 20 alkoxycarbonyl stands for methoxycarbonyl, ethoxycarbonyl, n-, i-propoxycarbonyl, n-, i-, sec.-, tert.-butoxycarbonyl, n-pentoxycarbonyl, n-hexoxycarbonyl, n-heptoxycarbonyl, n-octoxycarbonyl, n-nonoxycarbonyl, n-decoxycarbonyl, n-undecoxycarbonyl, n-dodecoxycarbonyl, n-tridecoxycarbonyl, n-tetradecoxycarbonyl, n-pentadecoxycarbonyl, n-hexadecoxycarbonyl, n-heptadecoxycarbonyl, n-octadecoxycarbonyl, n-nonadecoxycarbonyl, n-eicosoxycarbonyl; hydroxyC 1
  • —COR 4 preferably may be —COMe
  • —COOR 5 preferably may be —COOH
  • —CONR 4 R 5 preferably may be —CONMe 2 ,
  • —SO 2 R 4 preferably may be —SO 2 Me
  • —SO 3 R 4 preferably may be —SO 3 H, resp. —SO 3 ⁇ ,
  • —SO 2 NR 4 R 5 preferably may be —SO 2 NMe 2 ,
  • —NR 4 R 5 preferably may be —NMe 2 .
  • Preferred embodiments of this invention are the following compositions which may comprise one of the resins and/or surfactants described below:
  • anionic, cationic, amphoteric or non-ionic surfactants can be chosen.
  • Anionic surfactants are e.g. alkyl-, aryl- or aralkyl sulphates or sulphonates; alkyl-, aryl- or aralkyl phosphates or phosphonates; or carboxylic acids.
  • Cationic surfactants which may be used are e.g. primary, secondary or tertiary amines or quaternary salts of amines, e.g. tallow trimethyl ammonium chloride.
  • Non-ionic surfactants which are suitable for use include e.g.
  • Amphoteric surfactants are e.g. betaines, glycinates, or propionates.
  • Surfactants are well-known in the art, e.g. from Surfactants Europa, Ed. Gordon L. Hellis, 3 rd edition, 1995, Royal Society of Chemistry, London.
  • compositions may be prepared by laking, with a magnesium, calcium, strontium, barium or maganese salt or a mixture of two or more of such salts,
  • Q is hydrogen, an alkali metal or ammonium, or
  • BONA 2-hydroxy-3-naphthoic acid
  • salts which can be used to effect laking are the chlorides, sulphates, nitrates, formates and acetates of magnesium, calcium, strontium, barium and manganese and mixtures of two or more thereof.
  • These laking metal salts may be added to the preformed azo dyestuff or mixture of azo dyestuffs, i.e. after the coupling reaction, or they may be included in the coupling reaction mixture, prior to coupling, together with the 2-hydroxy-3-naphthoic acid coupling component or, more usually, together with the diazonium salt or salts.
  • the coupling and laking reactions may be carried out using known procedures such as described in Industrial Organic Pigments, 2 nd edition, VCH, Weinheim, 1995, e.g. p. 604 to 606.
  • a solution or suspension of the diazonium salt may be added to a solution or suspension of the coupling component, or the coupling component solution or suspension may be added to the diazonium salt solution or suspension, or both diazonium salt solution or suspension and coupling component solution or suspension may be added simultaneously to water, to an aqueous buffer or to an aqueous solution of the metal salt used to effect laking.
  • the pH of the coupling reaction mixture is preferably maintained at from 9 to 12.
  • the surfactant and/or the resin can be added together or separately before or after coupling to the coupling or diazotisation component vessel.
  • the diazonium slurry optionally comprising a surfactant, and a 2-hydroxy-3-naphthoic acid solution, optionally comprising a resin and optionally a surfactant and obtainable e.g. in mixing 2-hydroxy-3-naphthoic acid, an aqueous solution of sodium hydroxide and optionally 2-hydroxynaphthalene, are added simultaneously to water having a temperature in the range of preferably 1 to 5° C. such that the pH usually remains in the range of from 9 to 12.
  • pH control is via addition of dilute sodium hydroxide solution.
  • the temperature is maintained at 3 to 10° C. by addition of ice.
  • the coupling reaction is carried out for 45 to 90 minutes.
  • the orange pigment slurry thus obtained is stirred for 10 to 30 minutes.
  • an aqueous solution of a magnesium, calcium, strontium, barium or manganese salt is added to the slurry.
  • the laking also can be carried out by adding the aqueous salt solution or a part of it during the diazotisation step.
  • the slurry preferably is then heated to a temperature in the range of from 50 to 90° C. and the pH usually is adjusted to 6 to 8 with preferably a dilute acid such as hydrochloride acid.
  • the pigment of the invention may be isolated by filtration from the reaction mixture when coupling and laking are completed.
  • the filtered product can be washed with water to remove soluble salts.
  • the pigment may be dried and powdered by sieving, ball-milling, grinding or other known methods.
  • Another embodiment of the present invention is related to the use of the inventive pigment composition for the preparation of coloring high molecular weight organic materials, preferably biopolymers, plastic materials, glasses, ceramic products, for formulations in decorative cosmetics, for the preparation of inks, preferably printing inks, gravure inks, offset inks, screen printing inks, security inks, stationary inks, coating inks, jet-inks, inks for stamp pads, inks for impact printing ribbons, inks for packaging printing; paint systems, in particular automotive lacquers, preferably on the base of high solid, waterborne, metallic paints, industrial paints, trade sales paints, coil coating and powder coating; non-impact printing material preferably for thermal wax transfer, ink-jet printing, thermal dye diffusion transfer; colored polymer particles preferably for color toners, particularly preferred for dry copy toners, such as smashed-type dry toners and polymerized-type dry toners, liquid copy toners, electrographic toners, preferably wet toners for
  • inventive pigment compositions are used as powder pigments, in the form of pigment preparations, master-batches and dry color.
  • preferred embodiments concern the use for the preparation of inks such as printing inks, gravure inks, offset inks, screen printing inks, flexo, security printing inks, coating inks, or jet-inks; inks for stationary, inks for stamp pads, inks for impact printing ribbons, and packaging printing; paints such as automobile paints preferably on the base of high solid, waterborne, metallic paints, industrial paints, trade sales paints, coil coating, powder coating, plastics, especially for laminations, fibres, sheet, and molded articles, non-impact printing material, e.g.
  • thermo wax transfer for thermal wax transfer, ink-jet printing, thermal dye diffusion transfer, colored polymer particles, especially dry copy toners, liquid copy toners, electrographic toners (i.e. charge generating and transport materials), as well as master batches for plastic coloration, master batches for toner coloration, color toners, color filters, preferably for the preparation of liquid crystal displays (LCD) and charge combined devices (CCD), cosmetics, in the biomedical field, for solar energy and collecting systems, and for coloring porous substrates.
  • LCD liquid crystal displays
  • CCD charge combined devices
  • suitable organic materials of high molecular weight having a molecular weight usually in the range of from 10 3 to 10 7 g/mol
  • vinyl polymers for example polystyrene, poly- ⁇ -methylstyrene, poly-p-methylstyrene, poly-p-hydroxystyrene, poly-p-hydroxy-phenylstyrene, polymethyl methacrylate and polyacrylamide as well as the corresponding methacrylic compounds, polymethylmaleate, polyacrylonitrile, polymethacrylonitrile, polyvinyl chloride, polyvinyl fluoride, polyvinylidene chloride, polyvinylidene fluoride, polyvinyl acetate, polymethyl vinyl ether and polybutyl vinyl ether; polymers which are derived from maleimide and/or maleic anhydride, such as copolymers of maleic anhydride with styrene; polyvinyl
  • cellulose, cellulose ethers and esters such as ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate, starch, chitin, chitosan, gelatin, zein; natural resins; synthetic resins such as alkyd resins, acrylic resins, phenolic resins, epoxide resins, aminoformaldehyde resins such as urea/-formaldehyde resins and melamine/formaldehyde resin; vulcanized rubber; casein; silicone and silicone resins; rubber, chlorinated rubber; and also polymers which are used, for example, as binders in paint systems, such as novolaks which are derived from C 1 -C 6 -aldehydes such as formaldehyde and acetaldehyde and a binuclear or mononuclear, preferably mononuclear, phenol which, if desired, is substituted by one or two C 1 -C 9 alkyl groups
  • Particularly preferred high molecular weight organic materials are, for example, cellulose ethers and esters, e.g. ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate, natural resins or synthetic resins (polymerization or condensation resins) such as aminoplasts, in particular urea/formaldehyde and melamine/formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polyamides, polyurethanes, polyester, ABS, ASA, polyphenylene oxides, vulcanized rubber, casein, silicone and silicone resins as well as their possible mixtures with one another.
  • cellulose ethers and esters e.g. ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate
  • natural resins or synthetic resins polymerization or condensation resins
  • aminoplasts in particular urea/formalde
  • organic materials in dissolved form as film formers, for example boiled linseed oil, nitrocellulose, alkyd resins, phenolic resins, melamine/formaldehyde and urea/formaldehyde resins as well as acrylic resins.
  • film formers for example boiled linseed oil, nitrocellulose, alkyd resins, phenolic resins, melamine/formaldehyde and urea/formaldehyde resins as well as acrylic resins.
  • Said high molecular weight organic compounds may be obtained singly or in admixture, for example in the form of granules, plastic materials, melts or in the form of solutions, in particular for the preparation of spinning solutions, paint systems, coating materials, inks or printing inks.
  • the novel pigment compositions are used for the mass coloration of polyvinyl chloride, polyamides and, especially, polyolefins such as polyethylene and polypropylene as well as for the preparation of paint systems, including powder coatings, inks, particularly printing inks, stationary inks, coating inks, jet-inks, color filters, toners, particularly electrophotographic toners, and coating colors.
  • Illustrative examples of preferred binders for paint systems are alkyd/melamine resin paints, acryl/melamine resin paints, cellulose acetate/cellulose butyrate paints and two-pack system lacquers based on acrylic resins which are crosslinkable with polyisocyanate.
  • the novel pigment compositions can be added in any desired amount to the material to be colored, depending on the end use requirements.
  • the pigments composition according to this invention can be used in an amount in the range from 0.01 to 40, preferably from 0.1 to 20% by weight, based on the total weight of the colored high molecular weight organic material.
  • composition comprising of
  • customary additives such as rheology improvers, dispersants, fillers, paint auxiliaries, siccatives, plasticizers, UV-stabilizers, and/or additional pigments or corresponding precursors in effective amounts, such as e.g. from 0 to 50% b.w., based on the total weight of (a) and (b).
  • the pigmenting of the high molecular weight organic materials with the novel pigment compositions is usually effected by incorporating said novel pigment compositions, if desired in the form of masterbatches, in the high molecular weight organic materials using customary apparatus suitable to this end, such as extruders, roll mills, mixing or milling apparatus.
  • the material thus treated is then normally brought into the desired final form by methods which are known per se, such as calandering, moulding, extrusion moulding, coating, casting, extruding, by injection moulding.
  • plasticizers can be added to the high molecular weight substances prior to moulding.
  • Plasticizers may be, for example, esters of phosphoric acid, phthalic acid and sebacic acid. Said plasticizers may be added before, during or after pigmenting the high molecular weight substances with the pigment compositions of this invention.
  • novel pigment compositions may advantageously be used in admixture with fillers, transparent and opaque white, colored and/or black pigments as well as customary luster pigments in the desired amount.
  • coating materials, color filters, toners, preferably electrophotographic toners, inks, particularly stationary inks, coating inks, printing inks, and jet-inks the corresponding high molecular weight organic substances, such as binders, synthetic resin dispersions etc. and the novel pigment compositions are usually dispersed or dissolved together, if desired together with customary additives such as dispersants, fillers, paint auxiliaries, siccatives, plasticizers and/or additional pigments or pigment precursors, in a common solvent or mixture of solvents. This can be achieved by dispersing or dissolving the individual components by themselves, or also several components together, and only then bringing all components together, or by adding everything together at once.
  • a further embodiment of the present invention relates to the use of the inventive pigment compositions for the preparation of dispersions and the corresponding dispersions, and paint systems, coating materials, color filters, inks, particularly printing inks such as thermal transfer-type printing inks, stationary inks, coating inks, jet-inks, toners, particularly toners for electrophotography such as smashed-type dry toners, polymerized-type dry toners, wet toners, comprising the inventive pigment compositions.
  • E.g. GB-A 2,182,165 describes the preparation of a color filter by sequential application of the red, blue and green pigments to a suitable substrate such as an amorphous silicon thin film transistor.
  • a suitable substrate such as an amorphous silicon thin film transistor.
  • a photolithographic technique whereby each pigment is deposited on a photoetched polymer surface and the pigment and polymer are removed from the un-irradiated areas by washing with a solvent.
  • the methods are known as dyeing methods, color resist methods, electron deposition methods and printing methods.
  • a pigment dispersion can be employed for color resist method, and kneading process using sand-mill or ball-mill can be applied to get the (micronized) pigment dispersion (see for example JP 4-37987 and JP 4-39041).
  • Another source which describes the preparation of color filters is given in U.S. Pat. No. 5,624,467.
  • An ink-jet printing ink can be prepared by mixing a pigment, a binder, water, an alcohol and additives.
  • binder polymers based on acrylate or methacrylate are preferred, particularly preferred are copolymers based on MMA/S, MMA/BA, ethylene-vinyl acetate, ethylene-vinyl acetate (partially hydrolyzed), ethylene-acrylate, ethylene-acrylic acid or combinations thereof.
  • a base is also preferred to increase the amount of solved polymer if water is used. Any kinds of base can be used and preferably water-soluble amines or sodium and potassium hydroxides are used.
  • the particle size of the pigment in ink-jet printing ink should be small and therefore, it is highly desired to disperse the above mixture by a skandex, a paint-shaker, or any kinds of a dispersing machine (see e.g. U.S. Pat. No. 4,597,794, EP-A 425,439 or U.S. Pat. No. 5,085,698).
  • the inventive pigment composition usually is dispersed in an organic solvent and is added into an aqueous surfactant solution while stirring.
  • the particle size of the toner is controlled by the stirring rate.
  • the solvent is changed from surfactant solution to the desirable solvent yielding the desired liquid toner.
  • the preparation of colored polymer particles can be carried out e.g. according to the methods described in Tokkai-Hei-S-100486 (suspension polymerization) or U.S. Pat. No. 4,077,804 (in situ polymerization) or by interface polymerization.
  • the inventive pigment compositions can be mixed with a monomer like styrene, yielding a dispersion, then the monomer usually is polymerized yielding the desired particles or toners.
  • Colored polymer particles can be used in the fields of toners (electrophotography), immunological diagnosis, spacer etc.
  • inventive pigment compositions can be admixed with various polymers such as flexible polyvinylchloride, polyethylene or polymethylmethacrylate in usual ways such as processing on a 2-roll mill. Tests carried out so far indicate that the inventive pigment compositions show excellent compatibility with the abovementioned polymers.
  • inventive pigment compositions relate to the use of the inventive pigment composition for the preparation of dispersions, paint systems, coating materials, color filters, inks, preferably printing inks, as well as color toners comprising the inventive pigment compositions.
  • inventive compositions provide considerably higher gloss than is seen with current liquid inks such as Pigment Orange 34 (e.g. IRGALITE® Orange F2G). Further, the inventive inks exhibit a superior fluidity and some of them are chlorine-free.
  • current liquid inks such as Pigment Orange 34 (e.g. IRGALITE® Orange F2G). Further, the inventive inks exhibit a superior fluidity and some of them are chlorine-free.
  • a third vessel containing a mixture of water (70 ml) and 47% aqueous sodium hydroxide solution (5.8 g) is heated to 80° C.
  • BEVIROS® 95 a tall oil resin manufactured by Bergvik Kemi AB
  • This is added to the second vessel just prior to coupling.
  • step (d) Into a fourth vessel is added water (250 ml) at 3° C.
  • the diazonium slurry obtained in step (a) and the rosin/2-hydroxy-3-naphthoic acid solution obtained in step (b) are then added simultaneously to this vessel such that the pH remains in the range of from 10.4 to 10.6.
  • pH control is via addition of dilute sodium hydroxide solution.
  • the temperature is maintained at 5 to 8° C. by addition of ice.
  • the coupling reaction is carried out for 1 hour.
  • the orange pigment slurry thus obtained is stirred for 15 minutes.
  • a 80% by weight solution of calcium chloride (17.2 g) in 100 ml water is added.
  • the slurry is then heated to 70° C. and the pH is adjusted to 7.2 with dilute hydrochloric acid, then filtered, afterwards washed with water and dried at 70° C. for 15 hours. Thereafter, the product is further heated for 4 hours at 90° C.
  • the resulting dried pigment is sieved through a 250 ⁇ m screen to give a powdered pigment composition.
  • composition of the resin vessel is as follows: BEVIROS® 95 (8.9 g), 47% aqueous sodium hydroxide solution (3.5 g) and water (140 ml).
  • step (d) The diazonium slurry obtained in step (a) is added to the rosin/2-hydroxy-3-naphthoic acid solution vessel.
  • the pH is maintained within the range of from 10.4 to 10.6 via addition of dilute sodium hydroxide solution.
  • the temperature is maintained at 5 to 8° C. by addition of ice.
  • the coupling reaction is carried out for 70 minutes.
  • the orange pigment slurry thus obtained is stirred for 60 minutes.
  • a 80% by weight solution of calcium chloride (17.2 g) in 100 ml water is added.
  • the slurry is then heated to 70° C. and the pH is adjusted to 7.2 with dilute hydrochloric acid, then filtered, afterwards washed with water and dried at 70° C. for 15 hours. Thereafter, the product is further heated for 4 hours at 90° C.
  • the resulting dried pigment is sieved through a 250 ⁇ m screen to give a powdered pigment composition.
  • the diazotisation reaction is then continued by dropwise addition of the remainder of the sodium nitrite solution over 35 minutes.
  • the temperature is maintained within a range of 3 to 5° C.
  • Addition of sodium nitrite is stopped when diazotisation is complete (as shown by no oxidant present to starch iodide paper).
  • a 80% by weight solution of calcium chloride (17.2 g) in 100 ml water is added.
  • a third vessel containing a mixture of water (100 ml) and 47% aqueous sodium hydroxide solution (1.78 g) is heated to 80° C.
  • BEVIROS® 95 (4.4 g) is added and stirred until dissolved. This is added to the second vessel just prior to coupling.
  • step (d) The diazonium slurry obtained in step (a) is added to the rosin/2-hydroxy-3-naphthoic acid solution vessel.
  • the pH is maintained within the range of from 10.4 to 10.6 via addition of dilute sodium hydroxide solution.
  • the temperature is maintained at 5 to 8° C. by addition of ice.
  • the coupling reaction is carried out for 60 minutes.
  • the orange pigment slurry thus obtained is stirred for 60 minutes.
  • the slurry is then heated to 70° C. and the pH is adjusted to 7.2 with dilute hydrochloric acid, then filtered, afterwards washed with water and dried at 70° C. for 15 hours. Thereafter, the product is further heated for 4 hours at 90° C.
  • the resulting dried pigment is sieved through a 250 ⁇ m screen to give a powdered pigment composition.
  • a third vessel containing a mixture of water (100 ml) and 47% aqueous sodium hydroxide solution (1.78 g) is heated to 80° C.
  • BEVIROS® 95 (4.4 g) is added and stirred until dissolved. This is added to the second vessel just prior to coupling.
  • step (d) Into a fourth vessel 250 ml of water of 3° C. are added. The diazonium slurry obtained in step (a) and the rosin/2-hydroxy-3-naphthoic acid solution are then added simultaneously to this vessel such that the pH remains in the range of from 10.4 to 10.6. Once addition of rosin/2-hydroxy-3-naphthoic acid solution is complete, pH control is via addition of dilute sodium hydroxide solution. The temperature is maintained at 5 to 8° C. by addition of ice.
  • the coupling reaction is carried out for 45 minutes.
  • the orange pigment slurry thus obtained is stirred for 40 minutes.
  • a solution of 80% by weight of calcium chloride (12.5 g) dissolved in 100 ml water is added.
  • the slurry is then heated to 70° C. and the pH is adjusted to 7.2 with dilute hydrochloric acid, then filtered, afterwards washed with water and dried at 70° C. for 15 hours. Thereafter, the product is further heated for 4 hours at 90° C.
  • the resulting dried pigment is sieved through a 250 ⁇ m screen to give a powdered pigment composition.
  • Printing inks are prepared by dispersing the pigment compositions obtained in examples 1 to 7 in an alcohol/nitrocellulose ink vehicle via a 16 hour ballmill:
  • a millbase is prepared by ball-milling 18% of the appropriate pigment composition and 82% of the ballmill medium for 16 hours.
  • the ballmill medium consists of 49% nitrocellulose medium and 51% ethanol.
  • After ball-milling is complete the millbase is reduced by addition of 50% by millbase weight of a reducing medium consisting of 24% maleic resin, 24% ethoxypropanol, 36% of nitrocellulose medium and 16% ethanol.
  • Flow is measured as the time taken to pass through a number 3 Zahn cup. The results quoted below are expressed as a percentage of the time taken for IRGALITE® Orange F2G to flow through the cup.

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EP1863887A1 (de) * 2005-03-19 2007-12-12 DyStar Textilfarben GmbH & Co. Deutschland KG Sicherheitskit und sicherheitstinte
JP4957045B2 (ja) * 2006-03-31 2012-06-20 東洋インキＳｃホールディングス株式会社 包装用印刷インキ組成物および該組成物を用いてなる包装材料
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CN103351709A (zh) * 2013-07-08 2013-10-16 苏州凹凸彩印厂 一种环保型无水胶印油墨
US10899660B2 (en) 2016-05-19 2021-01-26 Apple Inc. Asymmetric chemical strengthening
TWI655160B (zh) * 2016-05-19 2019-04-01 美商蘋果公司 非對稱化學強化
AU2017290253B2 (en) 2016-06-29 2021-11-25 Armstrong World Industries, Inc. High performance coatings for building panels
US11639307B2 (en) 2018-07-13 2023-05-02 Apple Inc. Patterned asymmetric chemical strengthening
US11447416B2 (en) 2018-12-20 2022-09-20 Apple Inc. Strengthened covers for electronic devices
JP6845958B1 (ja) 2020-05-26 2021-03-24 東洋インキＳｃホールディングス株式会社 水性インクジェットインキ及びインクジェット印刷物の製造方法
JP6845957B1 (ja) * 2020-05-26 2021-03-24 東洋インキＳｃホールディングス株式会社 水性インクジェットインキセット、及び、印刷物の製造方法
CA3200806A1 (en) 2020-12-03 2022-06-09 Michelle X. Wang Antimicrobial and antiviral building panels
US12408282B2 (en) 2022-01-19 2025-09-02 Apple Inc. Electronic devices having differentially strengthened cover members

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US2694055A (en) 1951-12-10 1954-11-09 Sherwin Williams Co Metallic azo pigments
US4083687A (en) 1975-07-04 1978-04-11 Ciba-Geigy Corporation Process for the dyeing of thermoplastics
EP0767219A2 (de) 1995-10-07 1997-04-09 Ciba SC Holding AG Pigmentierte Plastikzusammensetzung
US5997628A (en) * 1998-06-08 1999-12-07 Engelhard Corporation Heat stable laked monoazo pigment compositions
WO2000026303A1 (en) * 1998-10-31 2000-05-11 Ciba Specialty Chemicals Holding Inc. Solid solutions of monoazo pigments
US6294012B1 (en) * 1999-11-15 2001-09-25 Engelhard Corporation High strength monoazo yellow pigment
US6387170B1 (en) * 2000-08-28 2002-05-14 Dominion Colour Corporation Heat stable orange laked monoazo pigment
US6402828B1 (en) * 1999-03-24 2002-06-11 Ciba Specialty Chemicals Corporation Azo lake pigment composition

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JPH0826243B2 (ja) * 1989-09-08 1996-03-13 東洋インキ製造株式会社 モノアゾレーキ顔料及び顔料分散組成物

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US2694055A (en) 1951-12-10 1954-11-09 Sherwin Williams Co Metallic azo pigments
US4083687A (en) 1975-07-04 1978-04-11 Ciba-Geigy Corporation Process for the dyeing of thermoplastics
EP0767219A2 (de) 1995-10-07 1997-04-09 Ciba SC Holding AG Pigmentierte Plastikzusammensetzung
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US20020096086A1 (en) 2002-07-25
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DE60112452D1 (de) 2005-09-08
MXPA02012790A (es) 2003-10-24
WO2002024817A1 (en) 2002-03-28
EP1319048A1 (de) 2003-06-18
DE60112452T2 (de) 2006-03-23
CN1458965A (zh) 2003-11-26
AU2002212239A1 (en) 2002-04-02
BR0114017A (pt) 2003-07-22
ATE301166T1 (de) 2005-08-15
EP1319048B1 (de) 2005-08-03

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